14-hydroxydihydronormorphinone derivatives

Novel N - (31 - methyl - 21 - butenyl) -, N-cyclopropylmethyl -, and N - cyclobutylmethyl - 14 - hydroxydihydronormorphinones and the physiologically acceptable acid addition salts are prepared by reacting the corresponding N-unsubstituted compound with an alkyl halide, sulphate or sulphonate, or by reacting the corresponding N-unsubstituted compound or an acetal derived thereof, such as the ethylenedioxy derivative, with the required carboxylic acid chloride or anhydride, reducing the N-carbonyl group in the resulting 6-keto(or protected keto) - 3 - acyloxy - N - acyl - 14 - hydroxydihydronormorphinan, and in the morphine product oxiding the 6-hydroxy group into a keto group or converting the 6-protected keto group to a 6-keto group respectively. Therapeutic compositions contain the above novel compounds or their physiologically acceptable acid addition salts as the active ingredient. The compositions are analgetics as well as narcotic antagonists and may be in the form of tablets, liquids, syrups, elixirs and suppositories.